219745-19-4Relevant articles and documents
Boron trifluoride mediated prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols
Isleyen, Alper,Dogan, Oezdemir
, p. 1427 - 1432 (2007/10/03)
A one-pot procedure was developed for the synthesis of 3-chloro-3- arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported. Georg Thieme Verlag Stuttgart.